CN113440418A - Dental polymerizable composition - Google Patents
Dental polymerizable composition Download PDFInfo
- Publication number
- CN113440418A CN113440418A CN202110295880.XA CN202110295880A CN113440418A CN 113440418 A CN113440418 A CN 113440418A CN 202110295880 A CN202110295880 A CN 202110295880A CN 113440418 A CN113440418 A CN 113440418A
- Authority
- CN
- China
- Prior art keywords
- meth
- acrylate
- polymerizable composition
- dental
- mass
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 64
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 74
- 150000003682 vanadium compounds Chemical class 0.000 claims abstract description 18
- 150000001451 organic peroxides Chemical class 0.000 claims abstract description 13
- 150000003585 thioureas Chemical class 0.000 claims abstract description 12
- 229910052720 vanadium Inorganic materials 0.000 claims description 10
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000000463 material Substances 0.000 abstract description 13
- -1 monomers Chemical class 0.000 description 63
- 239000002253 acid Substances 0.000 description 21
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical group [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 11
- 239000000945 filler Substances 0.000 description 10
- 235000011180 diphosphates Nutrition 0.000 description 9
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 6
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 150000003512 tertiary amines Chemical class 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 3
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 3
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- UDXXYUDJOHIIDZ-UHFFFAOYSA-N 2-phosphonooxyethyl prop-2-enoate Chemical compound OP(O)(=O)OCCOC(=O)C=C UDXXYUDJOHIIDZ-UHFFFAOYSA-N 0.000 description 3
- UXTGJIIBLZIQPK-UHFFFAOYSA-N 3-(2-prop-2-enoyloxyethyl)phthalic acid Chemical compound OC(=O)C1=CC=CC(CCOC(=O)C=C)=C1C(O)=O UXTGJIIBLZIQPK-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 3
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical group OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229930006711 bornane-2,3-dione Natural products 0.000 description 3
- 229910021485 fumed silica Inorganic materials 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- DQMWMUMCNOJLSI-UHFFFAOYSA-N n-carbamothioylbenzamide Chemical compound NC(=S)NC(=O)C1=CC=CC=C1 DQMWMUMCNOJLSI-UHFFFAOYSA-N 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellityc acid Natural products OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- FSJSYDFBTIVUFD-SUKNRPLKSA-N (z)-4-hydroxypent-3-en-2-one;oxovanadium Chemical compound [V]=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FSJSYDFBTIVUFD-SUKNRPLKSA-N 0.000 description 2
- JAEZSIYNWDWMMN-UHFFFAOYSA-N 1,1,3-trimethylthiourea Chemical compound CNC(=S)N(C)C JAEZSIYNWDWMMN-UHFFFAOYSA-N 0.000 description 2
- FPZXQVCYHDMIIA-UHFFFAOYSA-N 1,1-diphenylthiourea Chemical compound C=1C=CC=CC=1N(C(=S)N)C1=CC=CC=C1 FPZXQVCYHDMIIA-UHFFFAOYSA-N 0.000 description 2
- PBGVARFFBCBNJT-UHFFFAOYSA-N 1,1-dipropylthiourea Chemical compound CCCN(C(N)=S)CCC PBGVARFFBCBNJT-UHFFFAOYSA-N 0.000 description 2
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 2
- RBGUKBSLNOTVCD-UHFFFAOYSA-N 1-methylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C RBGUKBSLNOTVCD-UHFFFAOYSA-N 0.000 description 2
- YEZOVIIHKKPUOS-UHFFFAOYSA-N 10-oxothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3S(=O)C2=C1 YEZOVIIHKKPUOS-UHFFFAOYSA-N 0.000 description 2
- UKLWSJHOTAABPK-UHFFFAOYSA-N 2-(7,7,9-trimethyl-2,4-dioxo-1,3,5-trioxacycloundec-6-yl)ethyl prop-2-enoate Chemical compound C1(=O)OC(C(CC(CCOC(O1)=O)C)(C)C)CCOC(C=C)=O UKLWSJHOTAABPK-UHFFFAOYSA-N 0.000 description 2
- LIZVXGBYTGTTTI-UHFFFAOYSA-N 2-[(4-methylphenyl)sulfonylamino]-2-phenylacetic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(C(O)=O)C1=CC=CC=C1 LIZVXGBYTGTTTI-UHFFFAOYSA-N 0.000 description 2
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 2
- KIWRLBQZUHYWJI-UHFFFAOYSA-N 2-[hydroxy(phenoxy)phosphoryl]oxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOP(=O)(O)OC1=CC=CC=C1 KIWRLBQZUHYWJI-UHFFFAOYSA-N 0.000 description 2
- ZLIOFIWIEHVBEV-UHFFFAOYSA-N 2-dihydroxyphosphinothioyloxyethyl prop-2-enoate Chemical compound P(=S)(OCCOC(C=C)=O)(O)O ZLIOFIWIEHVBEV-UHFFFAOYSA-N 0.000 description 2
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 2
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 2
- IGAWKPMXUGZZIH-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC(=O)C=C IGAWKPMXUGZZIH-UHFFFAOYSA-N 0.000 description 2
- QNZLVOCZGYXWKB-UHFFFAOYSA-N 4-dihydroxyphosphinothioyloxybutyl prop-2-enoate Chemical compound P(OCCCCOC(C=C)=O)(O)(O)=S QNZLVOCZGYXWKB-UHFFFAOYSA-N 0.000 description 2
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 2
- PDQAZBWRQCGBEV-UHFFFAOYSA-N Ethylenethiourea Chemical compound S=C1NCCN1 PDQAZBWRQCGBEV-UHFFFAOYSA-N 0.000 description 2
- 206010020751 Hypersensitivity Diseases 0.000 description 2
- GWJZBXZSVPXWFD-UHFFFAOYSA-N P(=S)(OCCCCCCCCCCCCCCOC(C=C)=O)(O)O Chemical compound P(=S)(OCCCCCCCCCCCCCCOC(C=C)=O)(O)O GWJZBXZSVPXWFD-UHFFFAOYSA-N 0.000 description 2
- WEDJZVNSPXQTNS-UHFFFAOYSA-N P(=S)(OCCCCCCOC(C=C)=O)(O)O Chemical compound P(=S)(OCCCCCCOC(C=C)=O)(O)O WEDJZVNSPXQTNS-UHFFFAOYSA-N 0.000 description 2
- DNRADZJJMMESFS-UHFFFAOYSA-N P(=S)(OCCCOC(C=C)=O)(O)O Chemical compound P(=S)(OCCCOC(C=C)=O)(O)O DNRADZJJMMESFS-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- MNOILHPDHOHILI-UHFFFAOYSA-N Tetramethylthiourea Chemical compound CN(C)C(=S)N(C)C MNOILHPDHOHILI-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- LWBJEGSVVQWSDF-UHFFFAOYSA-N [3-oxo-3-(10-prop-2-enoyloxydecoxy)propyl]phosphonic acid Chemical compound OP(O)(=O)CCC(=O)OCCCCCCCCCCOC(=O)C=C LWBJEGSVVQWSDF-UHFFFAOYSA-N 0.000 description 2
- MRCMTIRVXOVDMR-UHFFFAOYSA-N [3-oxo-3-(5-prop-2-enoyloxypentoxy)propyl]phosphonic acid Chemical compound OP(O)(=O)CCC(=O)OCCCCCOC(=O)C=C MRCMTIRVXOVDMR-UHFFFAOYSA-N 0.000 description 2
- LIPZALUJBHGKGU-UHFFFAOYSA-N [3-oxo-3-(6-prop-2-enoyloxyhexoxy)propyl]phosphonic acid Chemical compound OP(O)(=O)CCC(=O)OCCCCCCOC(=O)C=C LIPZALUJBHGKGU-UHFFFAOYSA-N 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 229940106691 bisphenol a Drugs 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 230000009610 hypersensitivity Effects 0.000 description 2
- DYYSJNQVLWANCC-UHFFFAOYSA-N oxolan-2-ylmethylthiourea Chemical compound NC(=S)NCC1CCCO1 DYYSJNQVLWANCC-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- NPUSTSBKXOLJIC-UHFFFAOYSA-N phenyl(2-prop-2-enoyloxyethoxy)phosphinic acid Chemical compound C=CC(=O)OCCOP(=O)(C1=CC=CC=C1)O NPUSTSBKXOLJIC-UHFFFAOYSA-N 0.000 description 2
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- 239000000068 pit and fissure sealant Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- SCNYCWQULCHALD-UHFFFAOYSA-N propyl 4-(dimethylamino)benzoate Chemical compound CCCOC(=O)C1=CC=C(N(C)C)C=C1 SCNYCWQULCHALD-UHFFFAOYSA-N 0.000 description 2
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- OVRQXQSDQWOJIL-UHFFFAOYSA-N 1,1-dibutylthiourea Chemical compound CCCCN(C(N)=S)CCCC OVRQXQSDQWOJIL-UHFFFAOYSA-N 0.000 description 1
- AZERQDZCGIDXHT-UHFFFAOYSA-N 1,1-dicyclohexylthiourea Chemical compound C1CCCCC1N(C(=S)N)C1CCCCC1 AZERQDZCGIDXHT-UHFFFAOYSA-N 0.000 description 1
- CNLHIRFQKMVKPX-UHFFFAOYSA-N 1,1-diethylthiourea Chemical compound CCN(CC)C(N)=S CNLHIRFQKMVKPX-UHFFFAOYSA-N 0.000 description 1
- ZQGWBPQBZHMUFG-UHFFFAOYSA-N 1,1-dimethylthiourea Chemical compound CN(C)C(N)=S ZQGWBPQBZHMUFG-UHFFFAOYSA-N 0.000 description 1
- XIBAZLLABMNRRJ-UHFFFAOYSA-N 1,4-di(propan-2-yl)benzene hydrogen peroxide Chemical compound OO.CC(C)C1=CC=C(C(C)C)C=C1 XIBAZLLABMNRRJ-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- VUVPNTYTOUGMDG-UHFFFAOYSA-N 1-(2-hydroxyethyl)-3-prop-2-enylthiourea Chemical compound OCCNC(=S)NCC=C VUVPNTYTOUGMDG-UHFFFAOYSA-N 0.000 description 1
- NQUXRXBRYDZZDL-UHFFFAOYSA-N 1-(2-prop-2-enoyloxyethyl)cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1(CCOC(=O)C=C)C(O)=O NQUXRXBRYDZZDL-UHFFFAOYSA-N 0.000 description 1
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 description 1
- HVQQISZSIDZXOH-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound ClC1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O.ClC1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O HVQQISZSIDZXOH-UHFFFAOYSA-N 0.000 description 1
- LPLFTYJAPSRTEJ-UHFFFAOYSA-N 10-dihydroxyphosphinothioyloxydecyl prop-2-enoate Chemical compound P(=S)(OCCCCCCCCCCOC(C=C)=O)(O)O LPLFTYJAPSRTEJ-UHFFFAOYSA-N 0.000 description 1
- CFKBCVIYTWDYRP-UHFFFAOYSA-N 10-phosphonooxydecyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCCCOP(O)(O)=O CFKBCVIYTWDYRP-UHFFFAOYSA-N 0.000 description 1
- FNNBMEPNLFQREK-UHFFFAOYSA-N 11-dihydroxyphosphinothioyloxyundecyl prop-2-enoate Chemical compound P(=S)(OCCCCCCCCCCCOC(C=C)=O)(O)O FNNBMEPNLFQREK-UHFFFAOYSA-N 0.000 description 1
- AQNYHJAPHQZCEG-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol methane Chemical compound C.OCC(CO)(CO)CO AQNYHJAPHQZCEG-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- UEKHZPDUBLCUHN-UHFFFAOYSA-N 2-[[3,5,5-trimethyl-6-[2-(2-methylprop-2-enoyloxy)ethoxycarbonylamino]hexyl]carbamoyloxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC(=O)NCCC(C)CC(C)(C)CNC(=O)OCCOC(=O)C(C)=C UEKHZPDUBLCUHN-UHFFFAOYSA-N 0.000 description 1
- FPKCTSIVDAWGFA-UHFFFAOYSA-N 2-chloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 FPKCTSIVDAWGFA-UHFFFAOYSA-N 0.000 description 1
- LDFUDVLWUQLNIS-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1.C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 LDFUDVLWUQLNIS-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- NGQFYOHQKIHSOQ-UHFFFAOYSA-N 2-ethoxyethyl prop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOCCOC(=O)C=C NGQFYOHQKIHSOQ-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- MIRQGKQPLPBZQM-UHFFFAOYSA-N 2-hydroperoxy-2,4,4-trimethylpentane Chemical compound CC(C)(C)CC(C)(C)OO MIRQGKQPLPBZQM-UHFFFAOYSA-N 0.000 description 1
- XRXANEMIFVRKLN-UHFFFAOYSA-N 2-hydroperoxy-2-methylbutane Chemical compound CCC(C)(C)OO XRXANEMIFVRKLN-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- QENRKQYUEGJNNZ-UHFFFAOYSA-N 2-methyl-1-(prop-2-enoylamino)propane-1-sulfonic acid Chemical compound CC(C)C(S(O)(=O)=O)NC(=O)C=C QENRKQYUEGJNNZ-UHFFFAOYSA-N 0.000 description 1
- AUZRCMMVHXRSGT-UHFFFAOYSA-N 2-methylpropane-1-sulfonic acid;prop-2-enamide Chemical compound NC(=O)C=C.CC(C)CS(O)(=O)=O AUZRCMMVHXRSGT-UHFFFAOYSA-N 0.000 description 1
- MYOZYAFLZCEDGG-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1.OS(=O)(=O)C=CC1=CC=CC=C1 MYOZYAFLZCEDGG-UHFFFAOYSA-N 0.000 description 1
- AMWPFXICICLPLF-UHFFFAOYSA-N 2-tert-butyl-4,6-dimethylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1.CC1=CC(C)=C(O)C(C(C)(C)C)=C1 AMWPFXICICLPLF-UHFFFAOYSA-N 0.000 description 1
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- AVCVRYFMUOYDFB-UHFFFAOYSA-N 5-dihydroxyphosphinothioyloxypentyl prop-2-enoate Chemical compound P(=S)(OCCCCCOC(C=C)=O)(O)O AVCVRYFMUOYDFB-UHFFFAOYSA-N 0.000 description 1
- IWGNGVPFYNULNK-UHFFFAOYSA-N 8-dihydroxyphosphinothioyloxyoctyl prop-2-enoate Chemical compound P(OCCCCCCCCOC(C=C)=O)(O)(O)=S IWGNGVPFYNULNK-UHFFFAOYSA-N 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
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- JVZHZVTVFIXIJF-UHFFFAOYSA-N N-carbamothioylbenzamide Chemical compound NC(=S)NC(=O)c1ccccc1.NC(=S)NC(=O)c1ccccc1 JVZHZVTVFIXIJF-UHFFFAOYSA-N 0.000 description 1
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- BTZNCZBIVDNMIY-UHFFFAOYSA-N P(=S)(OCCCCCCCCCCCCOC(C=C)=O)(O)O Chemical compound P(=S)(OCCCCCCCCCCCCOC(C=C)=O)(O)O BTZNCZBIVDNMIY-UHFFFAOYSA-N 0.000 description 1
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- 229910019142 PO4 Inorganic materials 0.000 description 1
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- AMFGWXWBFGVCKG-UHFFFAOYSA-N Panavia opaque Chemical compound C1=CC(OCC(O)COC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OCC(O)COC(=O)C(C)=C)C=C1 AMFGWXWBFGVCKG-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- 208000002599 Smear Layer Diseases 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 229910021542 Vanadium(IV) oxide Inorganic materials 0.000 description 1
- ULQMPOIOSDXIGC-UHFFFAOYSA-N [2,2-dimethyl-3-(2-methylprop-2-enoyloxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)(C)COC(=O)C(C)=C ULQMPOIOSDXIGC-UHFFFAOYSA-N 0.000 description 1
- QUEDYRXQWSDKKG-UHFFFAOYSA-M [O-2].[O-2].[V+5].[OH-] Chemical compound [O-2].[O-2].[V+5].[OH-] QUEDYRXQWSDKKG-UHFFFAOYSA-M 0.000 description 1
- HPLXJFZCZSBAAH-UHFFFAOYSA-N [V+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] Chemical compound [V+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] HPLXJFZCZSBAAH-UHFFFAOYSA-N 0.000 description 1
- ZZRNJMAKTWOSPG-UHFFFAOYSA-N [V+3].CCC[O-].CCC[O-].CCC[O-] Chemical compound [V+3].CCC[O-].CCC[O-].CCC[O-] ZZRNJMAKTWOSPG-UHFFFAOYSA-N 0.000 description 1
- YERWCDXTMWTOEL-UHFFFAOYSA-N [[6-[[3-hydroxy-2-(hydroxymethyl)propanoyl]oxyamino]-3,5,5-trimethylhexyl]amino] 3-hydroxy-2-(hydroxymethyl)propanoate Chemical compound OCC(CO)C(=O)ONCCC(C)CC(C)(C)CNOC(=O)C(CO)CO YERWCDXTMWTOEL-UHFFFAOYSA-N 0.000 description 1
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 1
- VBKRXPZQAMBGCG-UHFFFAOYSA-N a805811 Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1.CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VBKRXPZQAMBGCG-UHFFFAOYSA-N 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- ARCGXLSVLAOJQL-UHFFFAOYSA-N anhydrous trimellitic acid Natural products OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical class C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 description 1
- 125000002362 bornane-2,3-dione group Chemical group 0.000 description 1
- ZHXZNKNQUHUIGN-UHFFFAOYSA-N chloro hypochlorite;vanadium Chemical compound [V].ClOCl ZHXZNKNQUHUIGN-UHFFFAOYSA-N 0.000 description 1
- MRIZMKJLUDDMHF-UHFFFAOYSA-N cumene;hydrogen peroxide Chemical compound OO.CC(C)C1=CC=CC=C1 MRIZMKJLUDDMHF-UHFFFAOYSA-N 0.000 description 1
- 239000003479 dental cement Substances 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 210000004268 dentin Anatomy 0.000 description 1
- VZWSFRSDSFFQPF-UHFFFAOYSA-N diphenylphosphanyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=C(C(=O)P(C2=CC=CC=C2)C2=CC=CC=C2)C(=CC(=C1)C)C.CC1=C(C(=O)P(C2=CC=CC=C2)C2=CC=CC=C2)C(=CC(=C1)C)C VZWSFRSDSFFQPF-UHFFFAOYSA-N 0.000 description 1
- PSYDSRLQABJJAD-UHFFFAOYSA-N dodecylthiourea Chemical compound CCCCCCCCCCCCNC(N)=S PSYDSRLQABJJAD-UHFFFAOYSA-N 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- LPROFRYXADJDIE-UHFFFAOYSA-N ethylthiourea Chemical compound CCNC(S)=N.CCNC(S)=N LPROFRYXADJDIE-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- DBQGARDMYOMOOS-UHFFFAOYSA-N methyl 4-(dimethylamino)benzoate Chemical compound COC(=O)C1=CC=C(N(C)C)C=C1 DBQGARDMYOMOOS-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
- ISGXOWLMGOPVPB-UHFFFAOYSA-N n,n-dibenzylaniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC=CC=1)CC1=CC=CC=C1 ISGXOWLMGOPVPB-UHFFFAOYSA-N 0.000 description 1
- HKJNHYJTVPWVGV-UHFFFAOYSA-N n,n-diethyl-4-methylaniline Chemical compound CCN(CC)C1=CC=C(C)C=C1 HKJNHYJTVPWVGV-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- DUSYNUCUMASASA-UHFFFAOYSA-N oxygen(2-);vanadium(4+) Chemical compound [O-2].[O-2].[V+4] DUSYNUCUMASASA-UHFFFAOYSA-N 0.000 description 1
- LXTZRIBXKVRLOA-UHFFFAOYSA-N padimate a Chemical compound CCCCCOC(=O)C1=CC=C(N(C)C)C=C1 LXTZRIBXKVRLOA-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- OPXKHRNUFSAYRB-UHFFFAOYSA-N phenylthiourea Chemical compound NC(=S)NC1=CC=CC=C1.NC(=S)NC1=CC=CC=C1 OPXKHRNUFSAYRB-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- QDLDWVRFBWSNPG-UHFFFAOYSA-N pyridin-2-ylthiourea Chemical compound NC(=S)Nc1ccccn1.NC(=S)Nc1ccccn1 QDLDWVRFBWSNPG-UHFFFAOYSA-N 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 150000003513 tertiary aromatic amines Chemical class 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical group NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- JBIQAPKSNFTACH-UHFFFAOYSA-K vanadium oxytrichloride Chemical compound Cl[V](Cl)(Cl)=O JBIQAPKSNFTACH-UHFFFAOYSA-K 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
- A61K6/887—Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- A61K6/889—Polycarboxylate cements; Glass ionomer cements
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
- A61K6/887—Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
- A61K6/61—Cationic, anionic or redox initiators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/30—Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
- A61K6/62—Photochemical radical initiators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/70—Preparations for dentistry comprising inorganic additives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/70—Preparations for dentistry comprising inorganic additives
- A61K6/71—Fillers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/831—Preparations for artificial teeth, for filling teeth or for capping teeth comprising non-metallic elements or compounds thereof, e.g. carbon
Landscapes
- Health & Medical Sciences (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plastic & Reconstructive Surgery (AREA)
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Biophysics (AREA)
- Dental Preparations (AREA)
Abstract
The invention provides a dental polymerizable composition having excellent storage stability. The dental polymerizable composition includes a first material containing a (meth) acrylate, a 5-valent vanadium compound, and a thiourea derivative, and a second material containing a (meth) acrylate and an organic peroxide.
Description
Technical Field
The present disclosure relates to a dental polymerizable composition.
Background
As a polymerizable composition that can be used even under wet conditions such as in the oral cavity in dental treatment, for example, a polymerizable composition including a first material containing a (meth) acrylate, a thiourea derivative and a vanadium compound and a second material containing a (meth) acrylate and an organic peroxide (organic peroxide) has been proposed (for example, see patent document 1).
Documents of the prior art
Patent document
Patent document 1: japanese laid-open patent publication No. 2012-51856
Disclosure of Invention
However, the hardenability of the polymerizable composition after long-term storage, that is, the storage stability (storage stability) of the polymerizable composition, is desired to be improved.
An object of one aspect of the present disclosure is to provide a polymerizable composition for dental use which is excellent in storage stability.
In one aspect of the present disclosure, a polymerizable dental composition includes a first material including a (meth) acrylate, a 5-valent vanadium compound, and a thiourea derivative, and a second material including a (meth) acrylate and an organic peroxide.
According to one aspect of the present disclosure, a dental polymerizable composition having excellent storage stability can be provided.
Detailed Description
Hereinafter, a mode for carrying out the present disclosure will be described.
< polymerizable composition for dental use >
The dental polymerizable composition of the present embodiment is a 2-dose dental polymerizable composition including a first component containing a (meth) acrylate, a 5-valent vanadium compound, and a thiourea derivative, and a second component containing a (meth) acrylate and an organic peroxide.
The first material and the second material may be in the form of a paste, for example.
The mass ratio of the first component to the second component of the dental polymerizable composition of the present embodiment is usually 10:1 to 1: 10.
The dental polymerizable composition of the present embodiment generally uses a first material and a second material in a mixed manner.
The dental polymerizable composition of the present embodiment is suitably used for dental cements, perceptual hypersensitivity inhibitors (sensifiers for hypersensitivities), dental sealants (dental sealants), and the like.
Hereinafter, components constituting the dental polymerizable composition of the present embodiment will be described.
[ meth (acrylic acid ester ]
In the context of the present description and claims, (meth) acrylate refers to compounds (e.g., monomers, oligomers, prepolymers) that include 1 or more methacryloxy groups and/or acryloxy groups (hereinafter referred to as (meth) acryloxy groups).
The (meth) acrylate may have an acid group or may have no acid group, and the (meth) acrylate included in the first material is preferably an acid group-free (meth) acrylate. This can improve the storage stability of the dental polymerizable composition of the present embodiment.
(meth) acrylate having no acid group)
The (meth) acrylate having no acid group preferably has 2 or more (meth) acryloyloxy groups.
Examples of the (meth) acrylate having no acid group include methyl (meth) acrylate, isopropyl (isopropyl) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, hydroxypropyl (hydroxypropyl) acrylate, tetrahydrofurfuryl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (2-hydroxypropyl) acrylate, and 2-hydroxypropyl (meth) acrylate, 2-methoxyethyl (meth) acrylate (2-methoxyethyl (meth) acrylate), 2-ethoxyethyl (meth) acrylate (2-ethoxyethyl) acrylate, (2-methylhexyl (meth) acrylate), 2-methylhexyl (meth) acrylate), 2-ethylhexyl (meth) acrylate (2-ethylhexyl (meth) acrylate), benzyl (meth) acrylate), 2-hydroxy-1,3-di (meth) acryloxypropane (2-hydroxy-1, 3-di) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate (diethylene glycol di (meth) acrylate), triethylene glycol di (meth) acrylate (butylene glycol di (meth) acrylate), and butylene glycol di (meth) acrylate, Neopentyl glycol di (meth) acrylate, 1,3-butanediol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, trimethylolethane tri (meth) acrylate, pentaerythritol methane tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, 1,3-butanediol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, and pentaerythritol tri (meth) acrylate, Bisphenol A diglycidyl (meth) acrylate (bisphenol-A diglycidyl (meth) acrylate), bis-2- (meth) acryloyloxyethyl-2,2,4-trimethylhexamethylene dicarbonate (di-2- (meth) acryloyloxyethyl-2,2,4-trimethylhexamethylene dicarbamate), 1,3,5-tris [1,3-bis { (meth) acryloyloxy } -2-propoxycarbonylaminohexane ] -1,3,5- (1H,3H,5H) triazine-2,4,6-trione (1,3,5-tris [1,3-bis { (meth) acryloxy } -2-propoxycarbonylaminohexane ] -1,3,5- (1H,3H,5H) triazine-2,4,6-trione), 2- (4-methacryloxy) hydroxyphenyl) phenyl Propane (2,2-bis [4- (3- (meth) acryloxy-2-hydroxyproyl) phenyl ] propane), N '- (2,2,4-trimethylhexamethylene) bis [2- (aminocarboxy) propane-1,3-diol ] tetramethylacrylate (N, N' - (2,2,4-trimethylhexamethylene) bis [2- (aminocarboxy) propane-1,3-diol ] tetramethylacrylate), and the like, and two or more kinds may be used in combination. Among these, 2-hydroxy-1,3-di (meth) acryloyloxypropane, di-2- (meth) acryloyloxyethyl-2,2,4-trimethylhexamethylene dicarbonate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, triethylene glycol di (meth) acrylate are preferably used from the viewpoint of the mechanical strength of a cured product of the dental polymerizable composition of the present embodiment.
The content of the acid group-free (meth) acrylate in the polymerizable composition for dental use of the present embodiment is preferably 10 to 95% by mass, and more preferably 15 to 80% by mass. When the content of the acid group-free (meth) acrylate in the polymerizable composition for dental use of the present embodiment is 10 mass% or more and 95 mass% or less, the workability of the polymerizable composition for dental use of the present embodiment can be improved.
(meth) acrylate having acid group)
Examples of the (meth) acrylate having an acid group include (meth) acrylates having a phosphate group, (meth) acrylates having a pyrophosphate group, (meth) acrylates having a thiophosphate group, (meth) acrylates having a carboxyl group, (meth) acrylates having a sulfonic acid group, and (meth) acrylates having a phosphonic acid group, and two or more kinds of these (meth) acrylates may be used in combination. Among these, from the viewpoint of solubility of a tooth surface staining layer (smear layer) and decalcification (decalcification) property of the dental polymerizable composition of the present embodiment, it is preferable to use a (meth) acrylate having a phosphate group or a thiophosphate group, particularly in view of adhesiveness to enamel.
Here, the (meth) acrylate having an acid group may have a plurality of acid groups.
Instead of the (meth) acrylate having an acid group, an acid chloride, an alkali metal salt, and an amine salt of the (meth) acrylate having an acid group may be used.
Examples of the (meth) acrylate having a phosphoric acid group include 2- (meth) acryloyloxyethyl dihydrogen phosphate, bis [2- (meth) acryloyloxyethyl ] hydrogen phosphate, 2- (meth) acryloyloxyethyl phenyl hydrogen phosphate, 6- (meth) acryloyloxyethyl phenyl hydrogen phosphate, 10- (meth) acryloyloxyethyl dihydrogen phosphate (10- (meth) acryloyloxyethyl dihydrogen phosphate), 1- (meth) acryloyloxypropyl 1-bis (2- (meth) acryloyloxyethyl) hydrogen phosphate, 3-di (meth) acryloxypropan-2-dihydrogenphosphate, 1,3-di (meth) acryloxypropanol-2-phenylphosphonate (1,3-di (meth) acryloxypropan-2-phenylphosphonate), bis [5- {2- (meth) acryloxyethoxycarbonyl } heptyl ] hydrogenphosphate (bis [5- {2- (meth) acryloxyethoxycarbonyl } hexyl ] hydroxyphenyl ] phosphate), and the like. Among them, 10-methacryloyloxydecyl dihydrogen phosphate is preferably used from the viewpoint of the adhesiveness of the dental polymerizable composition of the present embodiment.
Examples of the (meth) acrylate having a pyrophosphate group include bis [2- (meth) acryloyloxyethyl ] pyrophosphate (bis (2- (meth) acryloyloxybutyl) pyrophosphate), bis [4- (meth) acryloyloxybutyl ] pyrophosphate (bis (4- (meth) acryloyloxybutyl) pyrophosphate), bis [6- (meth) acryloyloxyhexyl ] pyrophosphate (bis (6- (meth) acryloyloxyhexyl) pyrophosphate), bis [8- (meth) acryloyloxyoctyl ] pyrophosphate (bis (8- (meth) acryloyloxyoctyl) pyrophosphate), bis [10- (meth) acryloyloxydecyl ] pyrophosphate (bis (10- (meth) acryloyloxysylcystyl) and the like.
Examples of the (meth) acrylate having a thiophosphoric acid group include 2- (meth) acryloyloxyethyl dihydrogen thiophosphate (2- (meth) acryloyloxyhexyl dihydrogen thiophosphate), 3- (meth) acryloyloxypropyl dihydrogen thiophosphate, 4- (meth) acryloyloxybutyl dihydrogen thiophosphate, 5- (meth) acryloyloxypentyl dihydrogen thiophosphate, 6- (meth) acryloyloxyhexyl dihydrogen thiophosphate, 7- (meth) acryloyloxyheptyl dihydrogen thiophosphate, 8- (meth) acryloyloxyoctyl dihydrogen thiophosphate, 9- (meth) acryloyloxynonyl dihydrogen thiophosphate, 10- (meth) acryloyloxydecyl dihydrogen thiophosphate, 11- (meth) acryloyloxyundecyl dihydrogen thiophosphate, 2- (meth) acryloyloxyethyl dihydrogen thiophosphate, 3- (meth) acryloyloxy-propyl dihydrogen thiophosphate, 4- (meth) acryloyloxybutyl thiophosphate, 5- (meth) acryloyloxy-pentyl-thio-phosphate, 6- (meth) acryloyloxyhexyl-hexyl-thio-phosphate, 7- (meth) acryloyloxyundecyl-thio phosphate, 2- (meth) acryloyloxy-undecyl-thio phosphate, 2- (meth) phosphorothioate, and 1- (meth) acryloyloxy-decyl-thio phosphate, 12- (meth) acryloyloxydodecyl thiophosphate, 13- (meth) acryloyloxytridecyl thiophosphate, 14- (meth) acryloyloxytetradecyl thiophosphate, 15- (meth) acryloyloxytentadecyl thiophosphate, 16- (meth) acryloyloxytexadecyl thiophosphate, 17- (meth) acryloyloxyteptadecyl thiophosphate, 18- (meth) acryloyloxytadecyl thiophosphate, 19- (meth) acryloyloxytetradecyl thiophosphate, 20- (meth) acryloyloxyticosyl thiophosphate, etc.
Examples of the (meth) acrylate having a carboxyl group include 4- (meth) acryloyloxyethyl trimellitic acid (4- (meth) acryloyloxyethyl trimetallic acid), 4- (meth) acryloyloxyethyl trimellitic anhydride (4- (meth) acryloyloxyethyl trimetallic anhydride), 4- (meth) acryloyloxydecyl trimellitic anhydride (4- (meth) acryloyloxydecyl trimellitic anhydride), 11- (meth) acryloyloxy-1, 1-undecyldicarboxyl (11- (meth) acryloyloxy-1, 1-undecarboxylic acid), 1,4-di (meth) acryloyloxydecyl pyromellitic acid (1, 4-acryloyloxy) pyromellitic acid (2- (meth) acryloyloxyethyl methacrylate), and 4- (meth) acryloyloxyethyl trimellitic anhydride (4- (meth) acryloyloxydecyl trimetallic acid (4-acryloyloxy) and 4-di (meth) acryloxyethyl methacrylate (2- (meth) acrylic acid, 2- (meth) acryloyloxyethylphthalic acid (2- (meth) acryloyloxyethylphthalic acid), 2- (meth) acryloyloxyethylhexahydrophthalic acid (2- (meth) acryloyloxyethylphthalic acid), and the like.
Examples of the (meth) acrylate having a sulfonic acid group include 2- (meth) acrylamido-2-methylpropanesulfonic acid (2- (meth) acrylamide-2-methylpropanesulfonic acid), styrenesulfonic acid (styrenesulfonic acid), and 2-ethanesulfonate (2-sulfoethyl (meth) acrylate).
Examples of the (meth) acrylate having a phosphonic acid group include 2- (meth) acryloyloxyethylphenylphosphonate (2- (meth) acryloyloxyethylphenylphosphonate), 5- (meth) acryloyloxypentyl-3-phosphonopropionate (5- (meth) acryloyloxypentyl-3-phosphonopropionate), 6- (meth) acryloyloxyhexyl-3-phosphonopropionate (6- (meth) acryloyloxyhexyl-3-phosphonopropionate), 10- (meth) acryloyloxydecyl-3-phosphonopropionate (10- (meth) acryloyloxydecyl-3-phosphonopropionate), 6- (meth) acryloyloxyhexyl-3-phosphonoacetate (6- (meth) acryloyloxyhexyl-3-phosphonoacetate), 10- (meth) acryloyloxydecyl-3-phosphonoacetate (10- (meth) acryloyloxydecyl-3-phosphonoacetate) and the like.
The content of the (meth) acrylate having an acid group in the polymerizable composition for dental use of the present embodiment is preferably 0.1 to 20% by mass, and more preferably 0.5 to 10% by mass. When the content of the (meth) acrylate having an acid group in the polymerizable composition for dental use of the present embodiment is 0.1% by mass or more, the adhesiveness of the polymerizable composition for dental use of the present embodiment to dentin can be further improved, and when the content is 20% by mass or less, the hardening property of the polymerizable composition for dental use of the present embodiment can be further improved.
< 5-valent vanadium Compound >
The vanadium compound having a valence of 5 functions as a polymerization accelerator.
The vanadium 5-valent compound is preferably soluble in the (meth) acrylate.
The vanadium 5 valent compound is preferably an organovanadium compound. This can improve the solubility of the 5-valent vanadium compound in the dental polymerizable composition of the present embodiment in the (meth) acrylate.
The vanadium 5-valent compound is preferably vanadium oxytrialkoxide (vanadia oxytrialkoxide). This can improve the storage stability of the dental polymerizable composition of the present embodiment.
Examples of the vanadium trihydrocarbyloxyoxide include vanadium triisopropoxide (vanadia oxytrisopropoxide), vanadium tripropoxide (vanadia oxytropoxide), and vanadium triethoxyoxide (vanadia oxytetrahydroxide).
Examples of the 5-valent vanadium compound other than vanadium trihydrocarbyloxyoxide include vanadium oxychloride (vanadiumoxytrichloride).
Further, the 5-valent vanadium compound may be used alone, or two or more kinds may be used in combination.
The content of the 5-valent vanadium compound in the dental polymerizable composition of the present embodiment is preferably 0.001 to 1% by mass, and more preferably 0.01 to 0.1% by mass. When the content of the vanadium compound having a valence of 5 in the polymerizable composition for dental use of the present embodiment is 0.001% by mass or more, the curability of the polymerizable composition for dental use of the present embodiment can be improved, and when the content is 1% by mass or less, the storage stability of the polymerizable composition for dental use of the present embodiment can be improved.
For the same reason as described above, the content of the 5-valent vanadium compound in the first material is preferably 0.002 to 2 mass%, more preferably 0.02 to 0.2 mass%.
< Thiourea derivatives >
The thiourea derivative functions as a reducing agent for the chemical polymerization initiator.
Examples of the thiourea derivatives include ethylene thiourea (ethylene thiourea), N-methyl thiourea (N-methylthiothiourea), N-ethyl thiourea (N-ethylthiourea), N-propylthiourea (N-propylthiourea), N-butylthiourea (N-butylthiourea), N-lauryl thiourea (N-laurylthiourea), N-phenylthiourea (N-phenylthiourea), N-cyclohexylthiourea (N-cyclohexylthiourea), N-dimethylthiourea (N, N-dimethylthiourea), N-diethylthiourea (N, N-diethylthiourea), N-dipropylthiourea (N, N-dipropylthiourea), N-dibutylthiourea (N, N-dibutylthiourea), N-dipropylthiourea (N, N-dipropylthiourea), N-diphenylthiourea (N, N-laurylthiourea), n-diphenylthiourea), N-dicyclohexylthiourea (N, N-dicyclohexylthiourea), trimethylthiourea (trimethylthiourea), tetramethylthiourea (tetramethylthiourea), N-acetylthiourea (N-acetylthiourea), n-benzoylthiourea (N-benzoyl thiourea), 1-allyl-3- (2-hydroxyethyl) -2-thiourea (1-allyl-3- (2-hydroxyethoxy) -2-thiourea), 1- (2-tetrahydrofurfuryl) -2-thiourea (1- (2-tetrahydrofurfuryl) -2-thiourea), N-tert-butyl-N '-isopropylthiourea (N-tert-butyl-N' -isopropylthiourea), 2-pyridylthiourea (2-pyridylthiourea), and the like, and two or more kinds may be used in combination. Among these, N-benzoylthiourea is preferably used from the viewpoint of curability of the dental polymerizable composition of the present embodiment.
The content of the thiourea derivative in the polymerizable composition for dental use of the present embodiment is preferably 0.1 to 5% by mass, and more preferably 0.1 to 1% by mass. When the content of the thiourea derivative in the polymerizable composition for dental use of the present embodiment is 0.1% by mass or more, the curability of the polymerizable composition for dental use of the present embodiment can be improved, and when the content is 5% by mass or less, the solubility of the (meth) acrylate of the thiourea derivative in the polymerizable composition for dental use of the present embodiment can be improved.
For the same reason as described above, the content of the thiourea derivative in the first agent is preferably 0.2 to 10% by mass, and more preferably 0.2 to 2% by mass.
< organic peroxide >
The organic peroxide functions as an oxidizing agent of the chemical polymerization initiator.
Examples of the organic peroxide include benzoyl peroxide (cumene hydroperoxide), cumene hydroperoxide (cumene hydroperoxide), t-butyl hydroperoxide (t-butyl hydroperoxide), t-amyl alcohol peroxide (t-amyl hydroperoxide), 1,3,3-tetramethylbutyl hydroperoxide (1,1,3,3-tetramethylbutyl hydroperoxide), 2,5-dimethyl-2,5-di (hydroperoxide) hexane (2,5-dimethyl-2,5-di (hydroperoxide) hexane), p-diisopropylbenzene hydroperoxide (p-isopropylbenzene hydroperoxide), p-methane hydroperoxide (p-methyl hydroperoxide), pinane hydroperoxide (pinane hydroperoxide), and the like, and two or more kinds of these may be used in combination. Among these, cumene hydroperoxide is preferably used for the hardening properties of the dental polymerizable composition of the present embodiment.
The content of the organic peroxide in the polymerizable composition for dental use of the present embodiment is preferably 0.01 to 5% by mass, and more preferably 0.1 to 2% by mass. When the content of the organic peroxide in the polymerizable composition for dental use of the present embodiment is 0.01% by mass or more, the curability of the polymerizable composition for dental use of the present embodiment can be improved, and when the content is 5% by mass or less, the working margin of the polymerizable composition for dental use of the present embodiment can be extended.
For the same reason as described above, the content of the organic peroxide in the second material is preferably 0.02 to 10% by mass, and more preferably 0.2 to 4% by mass.
< other ingredients >
The first charge agent may also contain a tertiary amine.
The tertiary amine functions as a reducing agent for the chemical polymerization initiator.
The tertiary amine may be any of aliphatic tertiary amines and aromatic tertiary amines, preferably aromatic tertiary amines, and particularly preferably alkyl p-dialkylaminobenzoates.
Examples of the aliphatic tertiary amine include N, N-dimethylaminoethyl methacrylate (N, N-dimethylethylenediamine), triethanolamine (triethanolamine), and the like.
Examples of the alkyl p-dialkylaminobenzoate include methyl p-dimethylaminobenzoate, ethyl p-dimethylaminobenzoate, propyl p-dimethylaminobenzoate, amyl p-dimethylaminobenzoate, isoamyl p-dimethylaminobenzoate, ethyl p-dimethylaminobenzoate, and propyl p-dimethylaminobenzoate.
Examples of tertiary aromatic amines other than alkyl p-dialkylaminobenzoates include 7-dimethylamino-4-methylcoumarin (7-dimethylamino-4-methylcoumarin), N-dimethylaniline (N, N-dimethylaniline), N-dibenzylaniline (N, N-dibenzylaniline), N-dimethyl-p-toluidine (N, N-dimethyl-p-toluidine), N-diethyl-p-toluidine (N, N-diethyl-p-toluidine), N-bis (2-hydroxyethyl) p-toluidine (N, N-bis (2-hydroxyethoxy) -p-toluidine), N,2,4,6-pentamethylaniline (N, 2,4, 6-pentatoluidine), N,2,4-tetramethylaniline (N, n,2, 4-tetramethyllaniline), N-diethyl-2,4,6-trimethylaniline (N, N-diethyl-2,4, 6-trimethyllaniline), and the like.
Here, the tertiary amine may be used alone, or two or more of them may be used in combination.
The first and/or second additives may further include a polymerization inhibitor, a photopolymerization initiator, a filler, and the like.
Examples of the polymerization inhibitor include dibutylhydroxytoluene (dibutyl hydroxytoluene), 6-tert-butyl-2,4-xylenol (6-tert-butyl-2,4-xylenol), 2,6-di-tert-butyl-p-cresol (2,6-di-tert-butyl-p-cresol), and two or more kinds thereof may be used in combination.
Examples of the photopolymerization initiator include camphorquinone (camphorquinone), phenylbis (2,4,6-trimethylbenzoyl) phosphine oxide (phenylbis (2,4,6-trimethylbenzoyl) phosphinide), 2,4, 6-trimethylbenzoyldiphenylphosphine (2,4, 6-trimethylbenzoyldiphenylphosphine), benzyl ketal (benzyl ketal), diacetyl ketal (diacetyl ketal), benzyl dimethyl ketal (benzyl dimethyl ketal), benzyl diethyl ketal (benzyl diethyl ketal), benzyl bis (2-methoxyethyl) ketal (2-methylhexyl) ketal), 4'-dimethyl (benzyl dimethyl ketal) (4,4' -dimethyl (benzyl dimethyl ketal), anthraquinone (chromaquinone), 1-chloroanthraquinone (1-chloroanthraquinone), 1-chloroanthraquinone (1-2-chloroanthraquinone (1, 2-chloroanthraquinone), 2-benzanthraquinone), 1-hydroxyanthraquinone (1-hydroxyanthraquinone), 1-methylanthraquinone (1-methyllanthraquinone), 2-ethylanthraquinone (2-ethyllanthraquinone), 1-bromoanthraquinone (1-bromoanthraquinone), thioxanthone (thioxanthone), 2-isopropylthioxanthone (2-isopropylthioxanthone), 2-nitrothioxanthone (2-nitrothioxanthone), 2-methylthiothioxanthone (2-methylthioxanthone), 2,4-dimethylthioxanthone (2,4-dimethylthioxanthone), 2,4-diethylthioxanthone (2,4-dimethylthioxanthone), 2,4-diisopropylthioxanthone (2, 4-dioxothioxanthone), 2-chlorothioxanthone (7-chlorothioxanthone), 2,4-diisopropylthioxanthone (2,4-dimethylthioxanthone), 2-chlorothioxanthone (7-chlorothioxanthone-10-fluoroxanthone (10-trifluoromethylthioxanthone), and mixtures thereof, Thioxanthone-10-oxide (thioxanthone-10-oxide), benzoin methyl ether (benzoin methyl ether), benzoin ethyl ether (benzoin ethyl ether), benzoin isopropyl ether (benzoin isopropyl ether), benzoin isobutyl ether (benzoin isopropyl ether), benzophenone (benzophenone), bis (4-dimethylaminophenyl) ketone, 4'-bis (diethylamino) phenyl ketone (4,4' -bis (diethylamino) benzophenone), and the like, and two of them may be used in combination.
Examples of the filler include anhydrous silicic acid powder, fumed silica (fumed silica), aluminum powder, and glass powder (for example, barium glass powder and fluoroaluminosilicate (fluoroaluminosilicate) glass powder). Two or more kinds may be used in combination.
Here, the filler may be treated with a surface treatment agent such as a silane coupling agent.
The content of the filler in the dental polymerizable composition of the present embodiment is preferably 4 to 90% by mass, and more preferably 15 to 80% by mass. When the content of the filler in the dental polymerizable composition of the present embodiment is 4% by mass or more, the mechanical strength of the hardened body of the dental polymerizable composition of the present embodiment can be improved, and when the content is 90% by mass or less, the workability of the dental polymerizable composition of the present embodiment can be improved.
[ examples ]
Examples of the present disclosure are described below, but the disclosure is not limited to the examples.
Examples 1 to 9 and comparative examples 1 to 3
(preparation of paste 1)
An acid-free methacrylate, a 5-valent vanadium compound, a thiourea derivative, a filler, a tertiary amine, a photopolymerization initiator, and a polymerization inhibitor were mixed in a ratio [ mass% ] shown in table 1 to obtain paste 1.
(preparation of paste 2)
A paste 2 was obtained by mixing an acid group-free methacrylate, an acid group-containing methacrylate, an organic peroxide, a filler and a polymerization inhibitor in the proportions [ mass% ] shown in table 1.
Here, the abbreviations shown in table 1 have the following meanings.
Bis-GMA 2,2-Bis [4- (3-methacryloyloxy-2-hydroxypropyl) phenyl ] propane (2,2-Bis [4- (3-methacryloyloxy-2-hydroxypropyl) phenyl ] propane)
UDMA Di-2-methacryloyloxyethyl-2,2,4-trimethylhexamethylene dicarbamate (di-2-methacryloyloxyethyl-2,2,4-trimethylhexamethylene dicarbamate)
EBDMA Ethoxylated bisphenol A dimethacrylate (Ethoxylated bisphenol-acrylate)
NPG neopentyl glycol dimethacrylate (Neoprene)
TEGDMA Triethylene glycol dimethacrylate (Triethylglycol dimethacrylate)
MDP 10-methacryloxydecyl dihydrogen phosphate (10-methacryloxydecyldihydrogenphosphate)
HOMS 2-methacryloyloxyethylsuccinic acid (2-methacryloyloxyethylsuccinic acid)
TIPOVO Triisopropoxyvanadia (vanadia oxytriisoproxide)
TPOVO vanadium oxytripropoxide (vanadia oxytriproxide)
TEOVO vanadium trioxide (vanadia)
VAA vanadium (IV) oxide (vanadyl acetylacetonate (bis (2, 4-pentanedioate))
NBTU benzoyl thiourea (N-benzoyl thiourea)
CHP cumene hydroperoxide (cumene hydroperoxide)
Filler 1 barium glass powder G018-053 UFO0.4 (manufactured by SCHOTT)
Filler 2 (hydrophobic fumed silica) AEROSILRX300 (manufactured by AEROSIL, Japan)
Filler 3 Anhydrous silicic acid powder RAF1000 (manufactured by Longsen)
EPA Ethyl p-dimethylaminobenzoate
CQ is camphorquinone
BHT dibutylhydroxytoluene
Then, the storage stability of the pastes 1 and 2 (polymerizable dental compositions) was evaluated.
(storage stability)
In order to evaluate the storage stability of the dental polymerizable composition, an accelerated test was performed. Specifically, pastes 1 and 2 were stored at 60 ℃ for 14 days. Next, the pastes 1 and 2 before and after storage were mixed at a mass ratio of 1:1, and then the hardening time was measured to evaluate the storage stability of the polymerizable composition for dental use. Specifically, the mixture of pastes 1 and 2 was packed in an acrylic ring having an inner diameter of 8mm and a thickness of 2mm, and then the temperature was measured using an infrared thermometer to obtain the curing time.
Further, the evaluation criteria of storage stability are as follows.
Preferably, the change in the curing time of the dental polymerizable composition before and after storage is 3 minutes or less
Good that the change in the curing time of the dental polymerizable composition before and after storage exceeds 3 minutes, but is 4 minutes or less
Failure that the change in the curing time of the dental polymerizable composition before and after storage exceeded 4 minutes
The results of evaluating the storage stability of the dental polymerizable composition are shown in tables 1 and 2.
TABLE 1
TABLE 2
From tables 1 and 2, it is clear that the polymerizable compositions for dental use of examples 1 to 9 have high storage stability.
In contrast, the polymerizable dental compositions of comparative examples 1 to 3 did not contain a vanadium compound having a valence of 5, but used vanadyl acetylacetonate paste 1 containing a vanadium compound having a valence of 4, and thus had low storage stability.
Claims (3)
1. A dental polymerizable composition, wherein,
the method comprises the following steps:
a first agent comprising a (meth) acrylate, a 5-valent vanadium compound, and a thiourea derivative; and
and a second agent comprising a (meth) acrylate and an organic peroxide.
2. The dental polymerizable composition according to claim 1,
the 5-valent vanadium compound is an organic vanadium compound.
3. The dental polymerizable composition according to claim 2,
the vanadium 5-valent compound is vanadium trihydrocarbyloxy oxide.
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| EP (1) | EP3884921A1 (en) |
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| EP2163234A1 (en) * | 2007-06-07 | 2010-03-17 | Tokuyama Dental Corporation | Dental filling/restoration kit |
| EP2425808A1 (en) * | 2010-09-03 | 2012-03-07 | GC Corporation | Polymerizable composition |
| EP3342393A1 (en) * | 2015-08-28 | 2018-07-04 | GC Corporation | Dental cement |
| CN108366910A (en) * | 2015-12-18 | 2018-08-03 | 可乐丽则武齿科株式会社 | Dental adhesive material is set with |
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| JP5363843B2 (en) | 2008-03-19 | 2013-12-11 | 株式会社トクヤマデンタル | Dental filling and repair kit |
| CN105101935B (en) * | 2013-03-28 | 2018-02-23 | 可乐丽则武齿科株式会社 | Solidification compound |
| JP2020053184A (en) | 2018-09-25 | 2020-04-02 | 東芝ライテック株式会社 | Illuminating device |
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- 2021-03-04 BR BR102021004159-5A patent/BR102021004159A2/en unknown
- 2021-03-11 AU AU2021201550A patent/AU2021201550B2/en active Active
- 2021-03-17 EP EP21163173.4A patent/EP3884921A1/en active Pending
- 2021-03-19 CN CN202110295880.XA patent/CN113440418B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2163234A1 (en) * | 2007-06-07 | 2010-03-17 | Tokuyama Dental Corporation | Dental filling/restoration kit |
| EP2425808A1 (en) * | 2010-09-03 | 2012-03-07 | GC Corporation | Polymerizable composition |
| EP3342393A1 (en) * | 2015-08-28 | 2018-07-04 | GC Corporation | Dental cement |
| CN108366910A (en) * | 2015-12-18 | 2018-08-03 | 可乐丽则武齿科株式会社 | Dental adhesive material is set with |
Also Published As
| Publication number | Publication date |
|---|---|
| BR102021004159A2 (en) | 2021-10-05 |
| AU2021201550A1 (en) | 2021-10-14 |
| AU2021201550B2 (en) | 2022-02-17 |
| EP3884921A1 (en) | 2021-09-29 |
| CN113440418B (en) | 2023-12-26 |
| US20210299000A1 (en) | 2021-09-30 |
| JP2021151969A (en) | 2021-09-30 |
| US11571368B2 (en) | 2023-02-07 |
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